HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(3-Benzyloxy-propyl)-6-trimethylstannanyl-pyrimidine-2-carbonitrile → 4-(3-Benzyloxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(3-Benzyloxy-propyl)-6-trimethylstannanyl-pyrimidine-2-carbonitrile | HCID 57839110 | — |
| Reactant | HCID 67058919 | HCID 67058919 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(3-Benzyloxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile | HCID 69047005 | 35% |
Reaction Steps
3-Bromo-N-methyl-5-trifluoromethyl-benzenesulphonamide (37 mg), 4-(3-benzyloxy-propyl)-6-trimethylstannanyl-pyrimidine-2-carbonitrile (40 mg) and dichlorobis(triphenylphosphine)palladium(II) (7 mg) in DMF (1 mL) were heated in a microwave to 180° C. for five minutes. The mixture was diluted with ethyl acetate (20 mL) and washed with water (3×20 mL). Organics were separated, dried over sodium sulphate, filtered, and solvent was removed under reduced pressure to yield crude product. Purification by preparative-HPLC afforded 4-(3-benzyloxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (16.5 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07589095B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-cea8956997bb4fe1b7e1730ec28de368 |
| Source note | uspto-grants-2009_09 |